A Game Plan for That Conversation You’ve Been Putting Off

Have you been putting off an important-but-difficult conversation? Perhaps you just can’t bring yourself to share some negative feedback with a peer. Or maybe you are hesitant to admit to something you did wrong. Either way, your dread is probably growing over time as you imagine worse and worse scenarios for how the conversation will play out. Carrying an issue without resolution is like carrying debt. You’ll eventually have to pay the principal (by having the difficult conversation), but the longer you wait, the more interest you’ll pay in anxiety and dread.

If the idea of having to pay anxiety interest isn’t enough, consider the other reasons to have the difficult conversation sooner rather than later. First, the longer you put off the conversation, the more obscured the facts will become. Without objective examples, the conversation is more likely to stray into emotional and judgmental territory. That will make it more excruciating than if you can stick to the facts.

Also, as you get further out from the events in question, the conversation will get more awkward. Feedback delivered well after the fact is likely to yield a response of “Why didn’t you tell me sooner?” Similarly, if you put off admitting guilt, your failure to come clean quickly might allow things to get further off track and create a bigger hole to dig out of. Delaying might also look like you were covering something up. In any case, waiting to share a difficult message can erode trust in a relationship, whereas sharing a difficult message before it snowballs can enhance trust.

One caveat: Although there are many good reasons to get a difficult conversation over with, there are a few situations where it might be best to wait. If the topic of conversation is an emotional one, it’s best to take some time to calm down and think through what you want to say. If you’re in a situation where you can’t afford to stall progress, wait until the immediate situation has passed, and then raise the issue with an explanation of your timing. For example, if you’re racing to meet a deadline, it might not be the time to give your colleague feedback that they are alienating everyone by being too direct. That feedback could wait until the urgent task is done, to avoid causing a blowup that takes everyone off track. But the deferral should be deliberate and temporary. In the majority of situations, you should have the difficult conversation as quickly as possible.

Before diving into your conversation, do a little soul-searching about what’s behind your procrastination. Often, you put off delivering a difficult message because you’re worried about embarrassing the other person or hurting their feelings. Here’s an example I like to use to demonstrate why that’s the wrong approach: If you see someone with spinach in their teeth and you refrain from saying something because you don’t want to embarrass them, you’ve set them up for more embarrassment as they go about their business. The kind thing to do is to casually point out the food lodged in their teeth. The same thing is true if your teammate is giving long-winded presentations, being too abrupt with others, or taking credit for someone else’s ideas. Not saying something allows the person to carry on damaging their brand, and possibly the team’s.

When you need to say something that will be uncomfortable for the receiver, focus your energy on delivering the message in the kindest way possible. If you demonstrate positive intent, deliver your message delicately, and leave room to hear the other person’s point of view, you’ll find that the conversation is less uncomfortable than you expected. Remember that withholding feedback that could help a coworker improve isn’t nice — it’s neglectful.

Another reason you might be avoiding the conversation is that you’re afraid of triggering an unpleasant defensive response. Fair enough. You can mitigate that risk by taking the time to plan what you want to say. Write down exactly how you would broach the subject, and then share your thoughts with someone you trust. As you reflect on your message, find ways to make it as objective as possible, so that you’ll be less likely to trigger defensiveness. Remove judgment-laden terms and stick to the facts. Replace “You were highly disrespectful of me in that meeting” with “You spoke over me on three occasions.” The more verifiable your position is, the more confident you can be that the conversation will stay professional.

Once you’re clear on your message, it might be worth giving the person a heads-up about what you’re planning to talk about. In my experience, people don’t like to be blindsided by difficult conversations. Send a brief message a couple of hours before you plan on raising the subject. You can say something as simple as, “I want to talk with you about your presentation on Tuesday.” Leave enough time for the person to collect their thoughts, but not so much that the person will catastrophize about what is to come. Removing the shock factor will reduce the chance of the conversation getting overheated.

It’s also important to boost your confidence by choosing a good spot for your difficult conversation. Although privacy might be your primary concern, there might be other considerations. If you’re worried about the person responding angrily, choose a meeting room with glass windows, so that you both will be visible to others. If you’re worried that one or both of you might become emotional, choose a location close to the restroom, so you can retreat and collect yourselves before returning to your desks. The same holds true for the timing of your message: When does it make the most sense to have the conversation?

When you get to the moment of truth, be as authentic as possible about your discomfort — your body language will tell the whole story anyway. You can say, “I should have shared this with you earlier, but I couldn’t find a way to say it without becoming upset.” You can also frame the conversation by saying, “I value you so much as a colleague and a friend, so I wanted to take the time to say this right.”

It’s possible that the difficult conversation will trigger an emotional reaction. That’s OK. If it happens, stay calm and take your cues from the other person. If your colleague starts to cry, offer a tissue and ask if it’s OK for you to continue. If the person gets angry, stay composed. As long as you don’t overreact, most people will prefer to carry on and get the uncomfortable conversation over with. In general, I don’t recommend that you call attention to the emotion directly. Instead, talk about the importance of the issue: “I know you care a lot about how the team perceives you. That’s why I wanted to tell you this.” If you let emotions derail the conversation, you’ll have to revisit it later, or live with an awkward silence as you try to pretend the conversation never happened. That just prolongs the agony you were trying to end.

Finally, the worst thing you can do after delivering an uncomfortable message is to end the conversation too quickly. If you leave while things are still fully charged, the dread will transfer to the next interaction. Let the conversation continue for a little while, until you’ve returned to a normal tenor.

Life is full of difficult conversations, particularly if you’re invested in having a great team at work. Postponing a difficult conversation only makes it worse. Get your head around what you need to say, be deliberate about when and where to have the conversation, and then keep calm and carry on. You’ll feel better once it’s over.